(E)-3-(4-Chloro­phen­yl)-1-(2,3,4-trichloro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Yeap, C.S.; Prasad, D.J.; Nayak, S.P.; Laxmana, K.

doi:10.1107/S1600536810053213

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o241

doi:10.1107/S1600536810053213

Open

access

(E)-3-(4-Chlorophenyl)-1-(2,3,4-trichlorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § D. Jagadeesh Prasad,^b Suresh P. Nayak ^b and K. Laxmana ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Mangalore, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 December 2010; accepted 18 December 2010; online 8 January 2011)

In the title chalcone derivative, C₁₅H₈Cl₄O, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 48.13 (11)°. In the crystal, molecules are arranged into columns and stacked down the a axis featuring possible weak aromatic π–π stacking interactions [centroid–centroid separation = 3.888 (2) Å].

Related literature

For general background to and applications of chalcone derivatives, see: Geiger & Conn (1945 ); Misra et al. (1971 ); Cole & Julian (1954 ); Aries (1972 ); Levine et al. (1979 ); Vranasi et al. (1996 ).

Experimental

Crystal data

C₁₅H₈Cl₄O
M_r = 346.01
Triclinic, P 1
a = 3.8879 (2) Å
b = 6.7510 (3) Å
c = 13.7788 (5) Å
α = 97.620 (2)°
β = 96.177 (2)°
γ = 92.017 (2)°
V = 355.93 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 296 K
0.76 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.574, T_max = 0.837
7510 measured reflections
3395 independent reflections
3183 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.06
3395 reflections
181 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1324 Friedel pairs
Flack parameter: −0.02 (5)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053213/hb5777sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053213/hb5777Isup2.hkl

checkCIF report

Comment top

Chalcones are natural biocides (Geiger & Conn, 1945) and also well known as intermediates in the synthesis of heterocyclic compounds which exhibit various biological activities (Misra et al., 1971). The presence of enone functional group in the chalcone molecule confers antibiotic activity upon it (Cole & Julian, 1954). This property is enhanced when substitution is made at the α-(nitro and bromo) and (bromo and hydroxylic-) positions (Aries, 1972). Chalcones are also reported to possess trypanocidal (Levine et al., 1979), anti-inflammatory and anticancer properties (Vranasi et al., 1996).

The C7=C8 double bond of the title compound (I) exists in an E-configuration (Fig. 1). The dihedral angle between the two benzene rings being 48.13 (11)°. In the crystal structure, the molecules are arranged into columns and stacked down a axis (Fig. 2).

Related literature top

For general background to and applications of chalcone derivatives, see: Geiger & Conn (1945); Misra et al. (1971); Cole & Julian (1954); Aries (1972); Levine et al. (1979); Vranasi et al. (1996).

Experimental top

2,3,4-Trichloroacetophenone (10 mmol) was dissolved in ethanol. Sodium hydroxide (5 ml, 30%) solution and 4-chlorobeldehyde (10 mmol) were then added to the resulting solution with continuous stirring. The stirring was continued for 4 h and was allowed to stand overnight. The reaction mass was then poured onto the crushed ice. The resulting solid was separated, filtered and dried. The compound was re-crystallized using ethanol and DMF mixture to yield yellow blocks. M.P.: 162–165 °C

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, viewed down the a axis, showing molecules stacked down a axis.

(E)-3-(4-Chlorophenyl)-1-(2,3,4-trichlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₈Cl₄O	Z = 1
M_r = 346.01	F(000) = 174
Triclinic, P1	D_x = 1.614 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8879 (2) Å	Cell parameters from 5499 reflections
b = 6.7510 (3) Å	θ = 3.0–30.0°
c = 13.7788 (5) Å	µ = 0.82 mm⁻¹
α = 97.620 (2)°	T = 296 K
β = 96.177 (2)°	Block, yellow
γ = 92.017 (2)°	0.76 × 0.33 × 0.22 mm
V = 355.93 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3395 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
T_min = 0.574, T_max = 0.837	k = −8→9
7510 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0435P)² + 0.0513P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3395 reflections	Δρ_max = 0.33 e Å⁻³
181 parameters	Δρ_min = −0.18 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1324 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (5)

Crystal data top

C₁₅H₈Cl₄O	γ = 92.017 (2)°
M_r = 346.01	V = 355.93 (3) Å³
Triclinic, P1	Z = 1
a = 3.8879 (2) Å	Mo Kα radiation
b = 6.7510 (3) Å	µ = 0.82 mm⁻¹
c = 13.7788 (5) Å	T = 296 K
α = 97.620 (2)°	0.76 × 0.33 × 0.22 mm
β = 96.177 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3395 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3183 reflections with I > 2σ(I)
T_min = 0.574, T_max = 0.837	R_int = 0.024
7510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.33 e Å⁻³
S = 1.06	Δρ_min = −0.18 e Å⁻³
3395 reflections	Absolute structure: Flack (1983), 1324 Friedel pairs
181 parameters	Absolute structure parameter: −0.02 (5)
3 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.18842 (18)	1.21292 (10)	−0.08423 (5)	0.05987 (19)
Cl2	1.09977 (14)	0.85687 (8)	0.46292 (4)	0.04498 (14)
Cl3	0.99789 (19)	0.85943 (10)	0.68403 (5)	0.05664 (17)
Cl4	0.67317 (19)	0.47391 (11)	0.75284 (5)	0.0645 (2)
O1	0.9846 (5)	0.3188 (3)	0.28530 (12)	0.0512 (4)
C1	0.5993 (6)	0.7313 (4)	0.00979 (16)	0.0407 (5)
H1A	0.6920	0.6148	−0.0180	0.049*
C2	0.4793 (7)	0.8687 (4)	−0.05019 (16)	0.0445 (5)
H2A	0.4894	0.8451	−0.1178	0.053*
C3	0.3445 (6)	1.0413 (4)	−0.00805 (17)	0.0399 (5)
C4	0.3247 (6)	1.0802 (4)	0.09119 (18)	0.0428 (5)
H4A	0.2311	1.1973	0.1179	0.051*
C5	0.4465 (6)	0.9424 (3)	0.15142 (15)	0.0386 (5)
H5A	0.4366	0.9685	0.2190	0.046*
C6	0.5836 (5)	0.7650 (3)	0.11160 (14)	0.0336 (4)
C7	0.7206 (6)	0.6183 (3)	0.17296 (15)	0.0369 (4)
H7A	0.8342	0.5133	0.1418	0.044*
C8	0.6995 (6)	0.6198 (3)	0.26870 (15)	0.0372 (4)
H8A	0.5872	0.7226	0.3021	0.045*
C9	0.8480 (6)	0.4641 (3)	0.32376 (14)	0.0348 (4)
C10	0.8101 (5)	0.4806 (3)	0.43238 (14)	0.0319 (4)
C11	0.9116 (5)	0.6485 (3)	0.50096 (15)	0.0309 (4)
C12	0.8730 (6)	0.6515 (3)	0.60100 (16)	0.0357 (4)
C13	0.7287 (6)	0.4796 (4)	0.63117 (16)	0.0384 (5)
C14	0.6308 (6)	0.3128 (3)	0.56447 (18)	0.0432 (5)
H14A	0.5364	0.1997	0.5856	0.052*
C15	0.6713 (6)	0.3117 (3)	0.46607 (16)	0.0384 (4)
H15A	0.6054	0.1972	0.4216	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0665 (4)	0.0563 (4)	0.0629 (4)	0.0105 (3)	0.0037 (3)	0.0313 (3)
Cl2	0.0504 (3)	0.0319 (2)	0.0539 (3)	−0.0034 (2)	0.0081 (2)	0.0100 (2)
Cl3	0.0731 (4)	0.0484 (3)	0.0425 (3)	0.0058 (3)	−0.0047 (3)	−0.0069 (2)
Cl4	0.0849 (5)	0.0797 (5)	0.0369 (3)	0.0232 (4)	0.0178 (3)	0.0231 (3)
O1	0.0688 (12)	0.0460 (9)	0.0405 (8)	0.0188 (9)	0.0118 (8)	0.0036 (7)
C1	0.0496 (13)	0.0391 (11)	0.0343 (10)	0.0064 (10)	0.0069 (9)	0.0059 (8)
C2	0.0545 (13)	0.0489 (12)	0.0309 (9)	0.0041 (11)	0.0054 (9)	0.0072 (9)
C3	0.0393 (11)	0.0390 (11)	0.0440 (11)	0.0012 (9)	0.0028 (9)	0.0170 (9)
C4	0.0469 (12)	0.0331 (10)	0.0504 (12)	0.0074 (9)	0.0096 (10)	0.0078 (9)
C5	0.0468 (12)	0.0374 (11)	0.0314 (9)	0.0025 (9)	0.0056 (9)	0.0027 (8)
C6	0.0355 (9)	0.0342 (9)	0.0323 (9)	0.0014 (8)	0.0054 (8)	0.0074 (7)
C7	0.0376 (10)	0.0379 (11)	0.0367 (10)	0.0050 (9)	0.0061 (8)	0.0085 (8)
C8	0.0388 (11)	0.0399 (11)	0.0348 (10)	0.0067 (9)	0.0057 (8)	0.0095 (8)
C9	0.0379 (10)	0.0357 (10)	0.0317 (9)	0.0035 (8)	0.0044 (8)	0.0073 (7)
C10	0.0347 (10)	0.0293 (9)	0.0334 (9)	0.0074 (8)	0.0047 (8)	0.0086 (7)
C11	0.0307 (9)	0.0281 (9)	0.0348 (9)	0.0051 (7)	0.0024 (7)	0.0079 (7)
C12	0.0372 (10)	0.0364 (10)	0.0332 (9)	0.0105 (8)	−0.0003 (8)	0.0045 (7)
C13	0.0409 (11)	0.0460 (12)	0.0318 (9)	0.0127 (9)	0.0046 (8)	0.0146 (8)
C14	0.0462 (12)	0.0397 (12)	0.0483 (12)	0.0046 (10)	0.0075 (10)	0.0203 (10)
C15	0.0469 (12)	0.0286 (10)	0.0388 (10)	−0.0008 (8)	0.0000 (9)	0.0063 (8)

Geometric parameters (Å, º) top

Cl1—C3	1.745 (2)	C6—C7	1.463 (3)
Cl2—C11	1.730 (2)	C7—C8	1.329 (3)
Cl3—C12	1.709 (2)	C7—H7A	0.9300
Cl4—C13	1.718 (2)	C8—C9	1.474 (3)
O1—C9	1.218 (3)	C8—H8A	0.9300
C1—C2	1.383 (3)	C9—C10	1.509 (3)
C1—C6	1.399 (3)	C10—C11	1.392 (3)
C1—H1A	0.9300	C10—C15	1.399 (3)
C2—C3	1.378 (3)	C11—C12	1.400 (3)
C2—H2A	0.9300	C12—C13	1.403 (3)
C3—C4	1.369 (3)	C13—C14	1.370 (4)
C4—C5	1.389 (3)	C14—C15	1.381 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.398 (3)	C15—H15A	0.9300
C5—H5A	0.9300

C2—C1—C6	121.0 (2)	C9—C8—H8A	118.8
C2—C1—H1A	119.5	O1—C9—C8	123.42 (18)
C6—C1—H1A	119.5	O1—C9—C10	118.57 (18)
C3—C2—C1	118.9 (2)	C8—C9—C10	117.92 (17)
C3—C2—H2A	120.6	C11—C10—C15	118.23 (18)
C1—C2—H2A	120.6	C11—C10—C9	124.79 (18)
C4—C3—C2	122.0 (2)	C15—C10—C9	116.95 (19)
C4—C3—Cl1	119.28 (18)	C10—C11—C12	121.51 (18)
C2—C3—Cl1	118.73 (17)	C10—C11—Cl2	119.60 (14)
C3—C4—C5	119.1 (2)	C12—C11—Cl2	118.87 (16)
C3—C4—H4A	120.5	C11—C12—C13	118.2 (2)
C5—C4—H4A	120.5	C11—C12—Cl3	120.83 (17)
C4—C5—C6	120.77 (19)	C13—C12—Cl3	120.94 (16)
C4—C5—H5A	119.6	C14—C13—C12	120.76 (19)
C6—C5—H5A	119.6	C14—C13—Cl4	118.73 (17)
C5—C6—C1	118.25 (19)	C12—C13—Cl4	120.51 (18)
C5—C6—C7	122.28 (18)	C13—C14—C15	120.4 (2)
C1—C6—C7	119.43 (18)	C13—C14—H14A	119.8
C8—C7—C6	126.72 (19)	C15—C14—H14A	119.8
C8—C7—H7A	116.6	C14—C15—C10	120.9 (2)
C6—C7—H7A	116.6	C14—C15—H15A	119.6
C7—C8—C9	122.32 (19)	C10—C15—H15A	119.6
C7—C8—H8A	118.8

C6—C1—C2—C3	0.4 (4)	C8—C9—C10—C15	127.9 (2)
C1—C2—C3—C4	−0.3 (4)	C15—C10—C11—C12	−0.9 (3)
C1—C2—C3—Cl1	−179.2 (2)	C9—C10—C11—C12	−178.96 (19)
C2—C3—C4—C5	0.5 (4)	C15—C10—C11—Cl2	177.53 (17)
Cl1—C3—C4—C5	179.44 (19)	C9—C10—C11—Cl2	−0.6 (3)
C3—C4—C5—C6	−0.8 (4)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C1	0.9 (3)	Cl2—C11—C12—C13	−178.29 (16)
C4—C5—C6—C7	178.7 (2)	C10—C11—C12—Cl3	−179.78 (17)
C2—C1—C6—C5	−0.7 (3)	Cl2—C11—C12—Cl3	1.8 (2)
C2—C1—C6—C7	−178.6 (2)	C11—C12—C13—C14	0.5 (3)
C5—C6—C7—C8	8.2 (4)	Cl3—C12—C13—C14	−179.62 (19)
C1—C6—C7—C8	−174.0 (2)	C11—C12—C13—Cl4	−179.80 (16)
C6—C7—C8—C9	−179.9 (2)	Cl3—C12—C13—Cl4	0.1 (3)
C7—C8—C9—O1	−3.7 (4)	C12—C13—C14—C15	−0.3 (3)
C7—C8—C9—C10	179.8 (2)	Cl4—C13—C14—C15	179.98 (19)
O1—C9—C10—C11	129.4 (2)	C13—C14—C15—C10	−0.5 (4)
C8—C9—C10—C11	−53.9 (3)	C11—C10—C15—C14	1.1 (3)
O1—C9—C10—C15	−48.7 (3)	C9—C10—C15—C14	179.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₅H₈Cl₄O
M_r	346.01
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	3.8879 (2), 6.7510 (3), 13.7788 (5)
α, β, γ (°)	97.620 (2), 96.177 (2), 92.017 (2)
V (Å³)	355.93 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.76 × 0.33 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.574, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	7510, 3395, 3183
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.06
No. of reflections	3395
No. of parameters	181
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18
Absolute structure	Flack (1983), 1324 Friedel pairs
Absolute structure parameter	−0.02 (5)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160.

References

Aries, R. (1972). French Patent 2 192 811. Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cole, W. & Julian, P. L. (1954). J. Org. Chem. 19, 131–138. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Geiger, W. B. & Conn, J. E. (1945). J. Am. Chem. Soc. 67, 112–116. CrossRef CAS Web of Science Google Scholar
Levine, B. F., Bethea, C. G., Thurmond, C. D., Lynch, R. T. & Bernstein, J. L. (1979). J. Appl. Phys. 50, 2523–2527. CrossRef CAS Web of Science Google Scholar
Misra, S. S., Tewari, R. S. & Nath, B. (1971). Indian J. Appl. Chem. 34, 260–264. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vranasi, P. R., Jen, A. K. Y., Chandrashekar, J., Namboothiri, I. N. N. & Ratna, A. (1996). J. Am. Chem. Soc. 118, 12443–12448. Google Scholar